US6525214B1ExpiredUtility

Therapeutic agent

Priority: May 13, 1991Filed: May 4, 1992Granted: Feb 25, 2003

Est. expiryMay 13, 2011(expired)· nominal 20-yr term from priority

Inventors:Bernard John Armitage Paul Frederick Coe

A61P 29/00A61P 25/04C07C 57/30A61K 31/19A61K 31/192

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Claims

Abstract

The use of S(−)sodium 2-(4-isobutylphenyl)-propionate (the sodium salt of S(+)-ibuprofen) in pharmaceutical compositions for the treatment of inflammation, pain and pyrexia is described. Preferred compositions comprise S(−)sodium 2-(4-isobutylphenyl)-propionate dihydrate. Processes to prepare S(−)sodium 2-(4-isobutylphenyl)propionate and its use in a process to prepare S(+) 2-(4-isobutylphenyl)propionic acid of high enantiomeric purity are also described.

Claims

exact text as granted — not AI-modified

What is claimed is:  
     
       1. A process for producing a substantially pure enantiomeric salt of 2-(4-isobutylphenyl)propionic acid which comprises: 
       (i) reacting said 2-(4-isobutylphenyl)propionic acid enriched with one of its enantiomers with a sodium containing base thereby forming a sodium salt of said 2-(4-isobutylphenyl)propionic acid enriched with said enantiomer;  
       (ii) treating said salt with a solvent;  
       (iii) separating a sodium salt of the substantially pure enantiomer of the 2-(4-isobutylphenyl)propionic acid.  
     
     
       2. The process according to  claim 1  wherein the sodium containing base is sodium hydroxide. 
     
     
       3. The process according to  claim 1  wherein the solvent for said treatment in step (ii) is an organic solvent. 
     
     
       4. The process according to  claim 1  wherein the ratio of said sodium containing base is from about 0.8 to about 1.1 mole per mole of enantiomerically enriched 2-(4-isobutylphenyl)propionic acid. 
     
     
       5. The process according to  claim 1  wherein the enantiomerically enriched 2-(4-isobutylphenyl)propionic acid is treated with said sodium containing base at a temperature of from about 5° C. to about 120° C. 
     
     
       6. A process for producing a substantially pure enantiomeric salt of 2-(4-isobutylphenyl)propionic acid which comprises: 
       (i) reacting in a solvent said 2-(4-isobutylphenyl)propionic acid enriched with one of its enantiomers with a sodium containing base and a separation enhancing amount of water thereby forming a hydrated sodium salt of said 2-(4-isobutylphenyl)propionic acid enriched with said enantiomer;  
       (ii) separating the hydrated sodium salt of the substantially pure enantiomer of the 2-(4-isobutylphenyl) propionic acid.  
     
     
       7. The process according to  claim 6  wherein the sodium containing base is sodium hydroxide. 
     
     
       8. The process according to  claim 6  wherein the solvent for said treatment in step (ii) is an organic solvent. 
     
     
       9. The process according to  claim 6  wherein the ratio of said sodium containing base is from about 0.8 to about 1.1 mole per mole of enantiomerically enriched 2-(4-isobutylphenyl) propionic acid. 
     
     
       10. The process according to  claim 6  wherein the enantiomerically enriched 2-(4-isobutylphenyl)propionic acid is treated with said sodium containing base at a temperature of from about 5° C. to about 120° C. 
     
     
       11. The process according to  claim 10  wherein the temperature is 40° C. to 60° C. 
     
     
       12. The process according to  claim 6 , wherein the mole ratio of said separation enhancing amount of water to the 2-(4-isobutylphenyl)propionic acid is greater than or equal to about 2. 
     
     
       13. The process according to  claim 6 , wherein the hydrated sodium salt is the dihydrated sodium salt of 2-(4-isobutylphenyl)propionic acid. 
     
     
       14. A process for producing a substantially pure enantiomeric salt of 2-(4-isobutylphenyl)propionic acid which comprises: 
       (i) reacting in a solvent said 2-(4-isobutylphenyl)propionic acid enriched with one of its enantiomers with sodium hydroxide and a separation enhancing amount of water thereby forming a hydrated sodium salt of said 2-(4-isobutylphenyl)propionic acid enriched with said enantiomer;  
       (ii) separating the hydrated sodium salt of the substantially pure enantiomer of the 2-(4-isobutylphenyl) propionic acid; and  
       (iii) treating said hydrated sodium salt of the substantially pure enantiomer of the 2-(4-isobutylphenyl) propionic acid to produce the substantially pure enantiomer of said 2-(4-isobutylphenyl)propionic acid.  
     
     
       15. The hydrated salt of a substantially pure enantiomeric salt of 2-(4-isobutylphenyl)propionic acid produced from the process comprising: 
       (i) reacting in a solvent a 2-(4-isobutylphenyl)propionic acid enriched with one of its enantiomers with a sodium containing base and a separation enhancing amount of water thereby forming a hydrated sodium salt of said 2-(4-isobutylphenyl)propionic acid enriched with said enantiomer;  
       (ii) separating the hydrated sodium salt of the substantially pure enantiomer of the 2-(4-isobutylphenyl) propionic acid.  
     
     
       16. The salt of according to  claim 15  which is the dihydrate.

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